US20220389149A1 - Composition and cured product of same - Google Patents
Composition and cured product of same Download PDFInfo
- Publication number
- US20220389149A1 US20220389149A1 US17/760,980 US202017760980A US2022389149A1 US 20220389149 A1 US20220389149 A1 US 20220389149A1 US 202017760980 A US202017760980 A US 202017760980A US 2022389149 A1 US2022389149 A1 US 2022389149A1
- Authority
- US
- United States
- Prior art keywords
- formula
- compound
- group
- polyol
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 90
- -1 polyol compound Chemical class 0.000 claims abstract description 148
- 229920005862 polyol Polymers 0.000 claims abstract description 79
- 239000012948 isocyanate Substances 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 32
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 239000004793 Polystyrene Substances 0.000 claims abstract description 8
- 229920002223 polystyrene Polymers 0.000 claims abstract description 8
- 150000003077 polyols Chemical class 0.000 claims description 54
- 239000011248 coating agent Substances 0.000 claims description 49
- 238000000576 coating method Methods 0.000 claims description 41
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 28
- 125000002947 alkylene group Chemical group 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 22
- 229920003023 plastic Polymers 0.000 claims description 20
- 239000004033 plastic Substances 0.000 claims description 20
- 229920001296 polysiloxane Polymers 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000000126 substance Substances 0.000 abstract description 24
- 239000000758 substrate Substances 0.000 abstract description 17
- 150000001721 carbon Chemical group 0.000 description 24
- 230000000475 sunscreen effect Effects 0.000 description 20
- 239000000516 sunscreening agent Substances 0.000 description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 229920005989 resin Polymers 0.000 description 14
- 239000011347 resin Substances 0.000 description 14
- 229920000515 polycarbonate Polymers 0.000 description 11
- 239000004417 polycarbonate Substances 0.000 description 11
- 239000005056 polyisocyanate Substances 0.000 description 11
- 229920001228 polyisocyanate Polymers 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 10
- 150000002009 diols Chemical class 0.000 description 10
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 9
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000003607 modifier Substances 0.000 description 7
- 229920005906 polyester polyol Polymers 0.000 description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 6
- 241000428199 Mustelinae Species 0.000 description 6
- 0 [1*]n1c(=O)n([2*])c(=O)n([3*])c1=O Chemical compound [1*]n1c(=O)n([2*])c(=O)n([3*])c1=O 0.000 description 6
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 150000002596 lactones Chemical class 0.000 description 6
- 230000014759 maintenance of location Effects 0.000 description 6
- 229920005749 polyurethane resin Polymers 0.000 description 6
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 125000005442 diisocyanate group Chemical group 0.000 description 5
- 239000004205 dimethyl polysiloxane Substances 0.000 description 5
- 239000010954 inorganic particle Substances 0.000 description 5
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 5
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011146 organic particle Substances 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 238000011084 recovery Methods 0.000 description 4
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 4
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 3
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 3
- CKCGJBFTCUCBAJ-UHFFFAOYSA-N 2-(2-ethoxypropoxy)propyl acetate Chemical compound CCOC(C)COC(C)COC(C)=O CKCGJBFTCUCBAJ-UHFFFAOYSA-N 0.000 description 3
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 description 3
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 3
- QMAQLCVJIYANPZ-UHFFFAOYSA-N 2-propoxyethyl acetate Chemical compound CCCOCCOC(C)=O QMAQLCVJIYANPZ-UHFFFAOYSA-N 0.000 description 3
- QMYGFTJCQFEDST-UHFFFAOYSA-N 3-methoxybutyl acetate Chemical compound COC(C)CCOC(C)=O QMYGFTJCQFEDST-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- JDKXMEMCBZBFPW-UHFFFAOYSA-N CC(C)(C)n1c(=O)n(CN=C=O)c(=O)n(COC#N)c1=O Chemical compound CC(C)(C)n1c(=O)n(CN=C=O)c(=O)n(COC#N)c1=O JDKXMEMCBZBFPW-UHFFFAOYSA-N 0.000 description 3
- AHWDQDMGFXRVFB-UHFFFAOYSA-N Cn1c(=O)n(C)c(=O)n(C)c1=O Chemical compound Cn1c(=O)n(C)c(=O)n(C)c1=O AHWDQDMGFXRVFB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 3
- 238000007654 immersion Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920001610 polycaprolactone Polymers 0.000 description 3
- 239000004632 polycaprolactone Substances 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 3
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 3
- 239000013638 trimer Substances 0.000 description 3
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 2
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 2
- ATOUXIOKEJWULN-UHFFFAOYSA-N 1,6-diisocyanato-2,2,4-trimethylhexane Chemical compound O=C=NCCC(C)CC(C)(C)CN=C=O ATOUXIOKEJWULN-UHFFFAOYSA-N 0.000 description 2
- QGLRLXLDMZCFBP-UHFFFAOYSA-N 1,6-diisocyanato-2,4,4-trimethylhexane Chemical compound O=C=NCC(C)CC(C)(C)CCN=C=O QGLRLXLDMZCFBP-UHFFFAOYSA-N 0.000 description 2
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 2
- CUVLMZNMSPJDON-UHFFFAOYSA-N 1-(1-butoxypropan-2-yloxy)propan-2-ol Chemical compound CCCCOCC(C)OCC(C)O CUVLMZNMSPJDON-UHFFFAOYSA-N 0.000 description 2
- STXQJDVOMPXMMW-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)butane Chemical compound CCCCOC(C)COC STXQJDVOMPXMMW-UHFFFAOYSA-N 0.000 description 2
- QWOZZTWBWQMEPD-UHFFFAOYSA-N 1-(2-ethoxypropoxy)propan-2-ol Chemical compound CCOC(C)COCC(C)O QWOZZTWBWQMEPD-UHFFFAOYSA-N 0.000 description 2
- QPHFJZRSMXHTAW-UHFFFAOYSA-N 1-[2-(2-methoxypropoxy)propoxy]butane Chemical compound CCCCOCC(C)OCC(C)OC QPHFJZRSMXHTAW-UHFFFAOYSA-N 0.000 description 2
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- LIYRYVJXMPWPAS-UHFFFAOYSA-N 1-methoxy-2-propoxypropane Chemical compound CCCOC(C)COC LIYRYVJXMPWPAS-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- RZXAHVCTRLTLNA-UHFFFAOYSA-N 2-(2-methoxypropoxy)-1-propoxypropane Chemical compound CCCOCC(C)OCC(C)OC RZXAHVCTRLTLNA-UHFFFAOYSA-N 0.000 description 2
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ZKCCKKDTLQTPKF-UHFFFAOYSA-N 2-ethoxy-1-methoxypropane Chemical compound CCOC(C)COC ZKCCKKDTLQTPKF-UHFFFAOYSA-N 0.000 description 2
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 2
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 2
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 2
- QSGQMGSGZGLURU-UHFFFAOYSA-N C.C.CC(C)(C)COC(=O)CO Chemical compound C.C.CC(C)(C)COC(=O)CO QSGQMGSGZGLURU-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 101000642347 Homo sapiens Splicing factor 45 Proteins 0.000 description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000004642 Polyimide Substances 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 102100036374 Splicing factor 45 Human genes 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 239000006096 absorbing agent Substances 0.000 description 2
- HZSIFDFXFAXICF-UHFFFAOYSA-N acetolactone Chemical compound O=C1CO1 HZSIFDFXFAXICF-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- VEZXCJBBBCKRPI-UHFFFAOYSA-N beta-propiolactone Chemical compound O=C1CCO1 VEZXCJBBBCKRPI-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 238000000691 measurement method Methods 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 229960000380 propiolactone Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- KMOUUZVZFBCRAM-OLQVQODUSA-N (3as,7ar)-3a,4,7,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1C=CC[C@@H]2C(=O)OC(=O)[C@@H]21 KMOUUZVZFBCRAM-OLQVQODUSA-N 0.000 description 1
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 1
- RTTZISZSHSCFRH-UHFFFAOYSA-N 1,3-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC(CN=C=O)=C1 RTTZISZSHSCFRH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- AAAWJUMVTPNRDT-UHFFFAOYSA-N 2-methylpentane-1,5-diol Chemical compound OCC(C)CCCO AAAWJUMVTPNRDT-UHFFFAOYSA-N 0.000 description 1
- QWGRWMMWNDWRQN-UHFFFAOYSA-N 2-methylpropane-1,3-diol Chemical compound OCC(C)CO QWGRWMMWNDWRQN-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SXFJDZNJHVPHPH-UHFFFAOYSA-N 3-methylpentane-1,5-diol Chemical compound OCCC(C)CCO SXFJDZNJHVPHPH-UHFFFAOYSA-N 0.000 description 1
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical compound C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052582 BN Inorganic materials 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- PZNSFCLAULLKQX-UHFFFAOYSA-N Boron nitride Chemical compound N#B PZNSFCLAULLKQX-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- KEBMPIFHPWXEHI-UHFFFAOYSA-N CC(C)(C)COC(=O)CO Chemical compound CC(C)(C)COC(=O)CO KEBMPIFHPWXEHI-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 229920000571 Nylon 11 Polymers 0.000 description 1
- 229920000299 Nylon 12 Polymers 0.000 description 1
- 229920003189 Nylon 4,6 Polymers 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- 229920000572 Nylon 6/12 Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- JNSHFFNQBOCKJC-UHFFFAOYSA-N O=c1n(CO)c(=O)n(CO)c(=O)n1CO Chemical compound O=c1n(CO)c(=O)n(CO)c(=O)n1CO JNSHFFNQBOCKJC-UHFFFAOYSA-N 0.000 description 1
- 229920006152 PA1010 Polymers 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- ORLQHILJRHBSAY-UHFFFAOYSA-N [1-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1(CO)CCCCC1 ORLQHILJRHBSAY-UHFFFAOYSA-N 0.000 description 1
- RJDOZRNNYVAULJ-UHFFFAOYSA-L [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[F-].[F-].[Mg++].[Mg++].[Mg++].[Al+3].[Si+4].[Si+4].[Si+4].[K+] RJDOZRNNYVAULJ-UHFFFAOYSA-L 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 229920001895 acrylonitrile-acrylic-styrene Polymers 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000002421 anti-septic effect Effects 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 229940064004 antiseptic throat preparations Drugs 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- JRPBQTZRNDNNOP-UHFFFAOYSA-N barium titanate Chemical compound [Ba+2].[Ba+2].[O-][Ti]([O-])([O-])[O-] JRPBQTZRNDNNOP-UHFFFAOYSA-N 0.000 description 1
- 229910002113 barium titanate Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical class C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KOPBYBDAPCDYFK-UHFFFAOYSA-N caesium oxide Chemical compound [O-2].[Cs+].[Cs+] KOPBYBDAPCDYFK-UHFFFAOYSA-N 0.000 description 1
- 229910001942 caesium oxide Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000002041 carbon nanotube Substances 0.000 description 1
- 229910021393 carbon nanotube Inorganic materials 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- PMHQVHHXPFUNSP-UHFFFAOYSA-M copper(1+);methylsulfanylmethane;bromide Chemical compound Br[Cu].CSC PMHQVHHXPFUNSP-UHFFFAOYSA-M 0.000 description 1
- JQZRVMZHTADUSY-UHFFFAOYSA-L di(octanoyloxy)tin Chemical compound [Sn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O JQZRVMZHTADUSY-UHFFFAOYSA-L 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007849 furan resin Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 238000009499 grossing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 239000006224 matting agent Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- OTLDLKLSNZMTTA-UHFFFAOYSA-N octahydro-1h-4,7-methanoindene-1,5-diyldimethanol Chemical compound C1C2C3C(CO)CCC3C1C(CO)C2 OTLDLKLSNZMTTA-UHFFFAOYSA-N 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920006396 polyamide 1012 Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920002530 polyetherether ketone Polymers 0.000 description 1
- 229920001601 polyetherimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005672 polyolefin resin Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- HBMJWWWQQXIZIP-UHFFFAOYSA-N silicon carbide Chemical compound [Si+]#[C-] HBMJWWWQQXIZIP-UHFFFAOYSA-N 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 230000005477 standard model Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
- C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
- C08G18/4638—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/4661—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3842—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring
- C08G18/3851—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen containing heterocyclic rings having at least one nitrogen atom in the ring containing three nitrogen atoms in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4202—Two or more polyesters of different physical or chemical nature
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4266—Polycondensates having carboxylic or carbonic ester groups in the main chain prepared from hydroxycarboxylic acids and/or lactones
- C08G18/4269—Lactones
- C08G18/4277—Caprolactone and/or substituted caprolactone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/61—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
- C08L75/04—Polyurethanes
- C08L75/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L85/00—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers
- C08L85/04—Compositions of macromolecular compounds obtained by reactions forming a linkage in the main chain of the macromolecule containing atoms other than silicon, sulfur, nitrogen, oxygen and carbon; Compositions of derivatives of such polymers containing boron
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
- C09D175/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/20—Diluents or solvents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
- C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2375/04—Polyurethanes
- C08J2375/06—Polyurethanes from polyesters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2475/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
- C08J2475/04—Polyurethanes
Definitions
- the present disclosure relates to a composition for polyurethane resin molding and a cured product of the same.
- the present application claims priority from the Japanese Patent Application No. 2019-168879, filed in Japan on Sep. 17, 2019, the contents of which are incorporated herein by reference.
- Polyurethane resins have flexibility, elasticity, and strength. Thus, compositions for polyurethane resin molding are used in coating agents and the like.
- the coating agents are used, for example, to cover plastic substrates constituting vehicle parts, electronic devices, and the like, and such a coating agent is required to form a coating having adhesion to the substrate, hardness, and scratch resistance properties.
- a coating agent include compositions described in Patent Documents 1 and 2.
- an object of the present disclosure is to provide a composition capable of forming a cured product having excellent adhesion to a substrate, hardness, scratch resistance, and chemical resistance.
- Another object of the present disclosure is to provide a cured product having excellent adhesion to a substrate, hardness, scratch resistance, and chemical resistance.
- Yet another object of the present disclosure is to provide vehicle parts having at least a portion of their surfaces is covered with a cured product having excellent adhesion to a substrate, hardness, scratch resistance, and chemical resistance.
- Still another object of the present disclosure is to provide a housing having at least a portion of its surface is covered with a cured product having excellent adhesion to a substrate, hardness, scratch resistance, and chemical resistance, and an electronic device including the housing.
- a polyurethane resin obtained by reacting a polyol compound having an isocyanurate skeleton with a polyisocyanate compound having an isocyanurate skeleton has excellent adhesion to a substrate, hardness, and scratch resistance, as well as excellent chemical resistance.
- the present disclosure was completed based on these findings.
- the present disclosure provides a composition containing a polyol compound (A) and an isocyanate compound (B), the polyol compound (A) containing a compound (a1) having a number average molecular weight calibrated with polystyrene standards of less than 800, the compound (a1) being represented by Formula (1):
- R 1 to R 3 are a group represented by Formula (1a):
- L 1 and L 2 each identical or different, represent an alkylene group having from 1 to 10 carbon atom(s), and m represents a number of 0 or greater, except m does not simultaneously take 0 for R 1 to R 3 , and a bond with a wavy line binds to a nitrogen atom in the formula;
- L 3 to L 5 each identical or different, represent a hydrogen atom, an NCO group, or an alkyl group having from 1 to 10 carbon atom(s) and having a group represented by Formula (2′), except L 3 to L 5 do not simultaneously take 0:
- L 6 and L 7 each identical or different, represent an alkylene group having from 1 to 10 carbon atom(s), and a bond with a wavy line binds to a carbon atom of the alkyl group having from 1 to 10 carbon atom(s) in L 3 to L 5 in Formula (2).
- the present disclosure also provides the composition described above, in which the polyol compound (A) further contains a polyol (a2) in an amount ranging from 0.01 to 1.5 parts by weight relative to 1 part by weight of the compound (a1), the polyol (a2) having a hydroxyl value (KOH mg/g) from 30 to 300.
- a polyol (a2) in an amount ranging from 0.01 to 1.5 parts by weight relative to 1 part by weight of the compound (a1), the polyol (a2) having a hydroxyl value (KOH mg/g) from 30 to 300.
- the present disclosure also provides the composition described above, in which an equivalent ratio of an NCO group in the isocyanate compound (B) to an OH group in the polyol compound (A), that is NCO/OH, is in a range from 0.2 to 2.0.
- the present disclosure also provides the composition described above, further containing a polysiloxane derivative (C) in an amount from 0.1 to 0.5 parts by weight relative to 100 parts by weight of a total of the polyol compound (A) and the isocyanate compound (B).
- the present disclosure also provides the composition described above, further containing a solvent represented by Formula (3):
- R 4 and R 6 each identical or different, represent a hydrogen atom or an alkyl group having from 1 to 5 carbon atom(s), R 5 represents an alkylene group having from 1 to 5 carbon atom(s), represents an integer of 1 or greater, and t represents 0 or 1, and when s is an integer of 2 or greater, each of a plurality of R 5 may be identical or different.
- the present disclosure also provides the composition described above, in which the composition is a coating agent.
- the present disclosure also provides a cured product of the composition described above.
- the present disclosure also provides a plastic molded product, having at least a portion of its surface being covered with a coating including the cured product described above.
- composition of the present disclosure can form a cured product having excellent adhesion to a substrate, hardness, scratch resistance, and chemical resistance.
- a coating agent to cover a substrate enables the substrate to have those properties described above.
- the plastic molded product having at least a portion of its surface being covered with the cured product of the composition of the present disclosure has high surface hardness, excellent scratch resistance and chemical resistance.
- the plastic cured product covering the surface does not cause the plastic cured product covering the surface to peel off or whiten, enabling the plastic molded product to retain excellent appearance, adhesion, hardness, and scratch resistance over a long period of time.
- composition of the present disclosure contains a polyol compound (A) and an isocyanate compound (B).
- the composition of the present disclosure may contain an additional component other than the above components.
- the polyol compound (A) is a compound having a plurality of hydroxyl groups.
- the polyol compound (A) contains at least a polyester polyol compound (a1) represented by Formula (1):
- R 1 to R 3 in the formula, each identical or different, are a group represented by Formula (1a):
- L 1 and L 2 each identical or different, represent an alkylene group having from 1 to 10 carbon atom(s), and m represents a number of 0 or greater, except m does not simultaneously take 0 for R 1 to R 3 , and a bond with a wavy line binds to a nitrogen atom in the formula.
- alkylene group having from 1 to 10 carbon atom(s) in L 1 and L 2 examples include linear or branched alkylene groups, such as a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, a trimethylene group, a butylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, a 1,1′-dimethylethylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a 2-ethylhexylene group, a nonylene group, and a decylene group.
- linear or branched alkylene groups such as a methylene group, a methylmethylene group, a dimethylmethylene group, an ethylene group, a propylene group, a trimethylene group, a butylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene
- L 1 is, among others, preferably an alkylene group having from 1 to 3 carbon atom(s).
- L 2 is, among others, preferably an alkylene group having from 1 to 8 carbon atom(s) and particularly preferably an alkylene group having from 4 to 6 carbon atoms.
- the alkylene group is preferably a linear alkylene group.
- m described above is an average value of the degree of polymerization for the unit indicated with parentheses in Formula (1a) and is a number of 0 or greater, for example, from 0 to 7, preferably from 0 to 4, more preferably from 0 to 3, even more preferably from 0 to 2, and particularly preferably from 1 to 2.
- the number average molecular weight of the compound (a1) (Mn, calibrated with polystyrene standards) is less than 800, preferably from 570 to 630, more preferably from 580 to 620, and even more preferably from 590 to 610.
- a molecular weight dispersity (weight average molecular weight Mw/number average molecular weight Mn) of the compound (a1) is preferably from 1.0 to 1.5, more preferably from 1.0 to 1.3, and even more preferably from 1.0 to 1.2.
- the hydroxyl value (KOH mg/g) of the compound (a1) is, for example, from 200 to 400, and in particular, from the viewpoint of improving the hardness and chemical resistance of the resulting cured product, the hydroxyl value is preferably from 260 to 300, more preferably from 270 to 290, and even more preferably from 275 to 285.
- the hydroxyl value can be measured by the hydroxyl value measurement method described in JIS-K1557.
- the compound (a1) can be produced, for example, by ring-opening polymerization of the lactone using the hydroxyl group of Formula (1′) below as a starting point.
- L 1 in Formula (1′) is the same as L 1 in Formula (1a).
- lactone examples include ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -valerolactone, and ⁇ -caprolactone.
- the polyol compound (A) may contain an additional polyol compound other than the compound (a1).
- additional polyol compound include polyester polyols other than the compound (a1), polyether polyols, and polycaprolactone polyols. These can be used alone, or in a combination of two or more.
- Examples of the additional polyol compound include a polyol (a2) with a hydroxyl value (KOH mg/g) from 30 to 300.
- the composition containing the polyol (a2) tends to improve the flexibility of the resulting cured product.
- the hydroxyl value (KOH mg/g) of the polyol (a2) is preferably from 30 to 300, more preferably from 40 to 270, and even more preferably from 50 to 250. With the hydroxyl value (KOH mg/g) of the polyol (a2) less than 30, the composition will be unlikely to achieve good scratch resistance and chemical resistance for the resulting cured product, and with the hydroxyl value (KOH mg/g) of the polyol (a2) exceeding 300, the composition will be unlikely to achieve sufficient flexibility for the resulting cured product.
- the hydroxyl value can be measured by the hydroxyl value measurement method described in JIS-K1557.
- the number average molecular weight of the compound (a2) (Mn, calibrated with polystyrene standards) is, for example, preferably from 400 to 2500, more preferably from 450 to 2400, even more preferably from 500 to 2300, and particularly preferably from 500 to 2200.
- the molecular weight dispersity (weight average molecular weight Mw/number average molecular weight Mn) of the polyol (a2) is, for example, from 1 to 3.
- the polyol (a2) is preferably a polycarbonate polyol, a polyester polyol, and/or a copolymer of these, and more preferably two hydroxy groups are contained in the molecule.
- the polycarbonate polyol can be obtained by reacting a carbonic acid derivative such as, for example, diphenyl carbonate, dimethyl carbonate, diethyl carbonate, or phosgene.
- a carbonic acid derivative such as, for example, diphenyl carbonate, dimethyl carbonate, diethyl carbonate, or phosgene.
- diol examples include aliphatic diols having no alicyclic skeleton, such as ethylene glycol, diethylene glycol, triethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, neopentyl glycol, 1,3-butanediol, 1,4-butanediol, 1,5-pentanediol, 2-methyl-1,5-pentanediol, 3-methyl-1,5-pentanediol, 1,6-hexanediol, 1,8-octanediol, 2-methyl-1,3-propane diol; aliphatic diols having an alicyclic skeleton, such as cyclohexanedimethanol, hydrogenated bisphenol A, hydrogenated bisphenol F, tricyclodecane dimethanol, and hydrogenated bisphenol A.
- aliphatic diols having no alicyclic skeleton such as ethylene glycol, di
- the polyester polyol can be obtained by ring-opening polymerization of the lactone or by reacting a diol with a dicarboxylic acid.
- polyester polyol polylactone polyol
- lactone polyol examples include ⁇ -acetolactone, ⁇ -propiolactone, ⁇ -butyrolactone, ⁇ -valerolactone, and ⁇ -caprolactone.
- diol examples include those similar to the diol to be used to form the polycarbonate polyol.
- dicarboxylic acid examples include oxalic acid, adipic acid, sebacic acid, fumaric acid, malonic acid, succinic acid, glutaric acid, azelaic acid, citric acid, 2,6-naphthalene dicarboxylic acid, phthalic acid, isophthalic acid, terephthalic acid, citraconic acid, 1,10-decanedicarboxylic acid, methyl hexahydrophthalic anhydride, hexahydrophthalic anhydride, methyl tetrahydrophthalic anhydride, and tetrahydrophthalic anhydride.
- the copolymer can be obtained by copolymerizing the lactone, diol, dicarboxylic acid, and carbonic acid derivative described above.
- the content of the polyol (a2) in the polyol compound (A) is not particularly limited, but from the viewpoint of improving the flexibility of the resulting cured product, the content is preferably from 0.01 to 1.5 parts by weight, more preferably from 0.03 to 1.2 parts by weight, even more preferably from 0.05 to 1.0 parts by weight, and particularly preferably from 0.08 to 0.9 parts by weight relative to 1 part by weight of the polyol compound (a1).
- the content of the polyol (a2) in the polyol compound (A) is not particularly limited, but from the viewpoint of improving the flexibility of the resulting cured product, the content is preferably from 0.01 to 2.5 mol, more preferably from 0.03 to 2.0 mol, even more preferably from 0.05 to 1.5 mol, and particularly preferably from 0.08 to 1.0 mol per mol of the polyol compound (a1).
- the number average molecular weight and the molecular weight dispersity of the polyol compound (A) can be measured with instruments and conditions described in Examples.
- the isocyanate compound (B) contains at least an isocyanate compound (b) represented by Formula (2):
- L 3 to L 5 each identical or different, represent a hydrogen atom, an NCO group, or an alkyl group having from 1 to 10 carbon atom(s) and having a group represented by Formula (2′), except L 3 to L 5 do not simultaneously take hydrogen atoms:
- L 6 and L 7 each identical or different, represent an alkylene group having from 1 to 10 carbon atom(s), and a bond with a wavy line binds to a carbon atom of the alkyl group having from 1 to 10 carbon atom(s) in L 3 to L 5 in Formula (2).
- the alkyl group having from 1 to 10 carbon atom(s) in the L 3 to L 5 described above is preferably an alkyl group corresponding to the alkylene group L 2 in Formula (1a).
- L 3 to L 5 described above are preferably an alkyl group having from 3 to 8 carbon atoms, and more preferably an alkyl group having from 4 to 8 carbon atoms.
- the alkyl group is preferably a linear alkyl group.
- Examples of the alkylene group having from 1 to 10 carbon atom(s) in L 6 and L 7 described above include linear or branched alkylene groups, such as a methylene group, an ethylene group, a trimethylene group, a propylene group, a dimethylmethylene group, an isopropylene group, a butylene group, a 1-methyltrimethylene group, a 2-methyltrimethylene group, a 1,1′-dimethylethylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a 2-ethylhexylene group, a nonylene group, and a decylene group.
- a linear alkylene group is preferred.
- the NCO content in the isocyanate compound (b) is, for example, from 17 to 25 wt. %, preferably from 18 to 24 wt. %, and more preferably from 19 to 23 wt. %.
- the isocyanate compound (B) may contain one, or two or more additional isocyanate compound(s) other than the isocyanate compound (b).
- additional isocyanate compound include aliphatic polyisocyanates, such as 1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,4,4-trimethylhexamethylene diisocyanate; trimers of the aliphatic polyisocyanate (excluding the isocyanate compound (b)); allophanates, biurets, or adducts of the aliphatic polyisocyanate; aromatic polyisocyanates, such as triylene diisocyanate, xylylene diisocyanate, and diphenylmethane diisocyanate; alicyclic polyisocyanates, such as polyisocianates obtained by hydrogenating an aromatic polyisocianate, 4,4′-dicyclohexylmethane diisocyanate, and isophorone
- the isocyanate compound (B) contains the isocyanate compound (b), for example, in an amount of preferably 60 wt. % or higher (more preferably 70 wt. % or higher, even more preferably 80 wt. % or higher, and particularly preferably 90 wt. % or higher) relative to the total amount of the isocyanate compound (B) from the viewpoint of improving the hardness and chemical resistance of the resulting cured product.
- the composition of the present disclosure contains a polyol compound (A) and an isocyanate compound (B).
- the equivalent ratio of the isocyanate group (NCO group) contained in the isocyanate compound (B) to the hydroxyl group (OH group) contained in the polyol compound (A), that is NCO/OH is preferably in a range from 0.2 to 2.0, more preferably from 0.5 to 1.5, even more preferably from 0.7 to 1.3, and particularly preferably from 0.9 to 1.2.
- the content of the isocyanate compound (B) in the composition is preferably from 40 to 140 parts by weight, more preferably from 50 to 130 parts by weight, and even more preferably from 60 to 120 parts by weight relative to 100 parts by weight of the polyol compound (A), from the viewpoint of improving the hardness and chemical resistance of the resulting cured product.
- composition of the present disclosure may further contain as necessary an inorganic particle, an organic particle, an additive, or the like.
- Inorganic particles that the composition of the present disclosure may further contain are not particularly limited, but examples include silica, alumina, mica, synthetic mica, talc, calcium oxide, calcium carbonate, zirconium oxide, titanium oxide, barium titanate, kaolin, bentonite, diatomaceous earth, boron nitride, aluminum nitride, silicon carbide, zinc oxide, cerium oxide, cesium oxide, magnesium oxide, glass beads, glass fibers, graphite, carbon nanotubes, calcium hydroxide, magnesium hydroxide, and aluminum hydroxide.
- silica is preferred.
- Organic particles that the composition of the present disclosure may further contain are not particularly limited, but examples include polyethylene wax, polypropylene wax, acrylic beads, and urethane beads. Among these, from the viewpoint of improving the texture (soft feel properties) of the coating film, a urethane bead is preferred.
- one type of these particles can be used alone or two or more types can be used in combination.
- the particle sizes of the inorganic particles and the organic particles are not particularly limited but are, for example, preferably from 0.01 nm to 1 ⁇ m from the viewpoint of good appearance.
- composition of the present disclosure may further contain include surfactants, pigments, dyes, ultraviolet absorbers, light stabilizers, surface modifiers, antifoaming agents, wetting agents, dispersants, viscoelasticity modifiers, thixotropy-imparting agents, antiseptics, film-forming agents, plasticizers, penetrants, perfumes, bactericides, fungicides, ultraviolet absorbers, antioxidants, antistatic agents, flame retardants, and matting agents.
- surfactants include surfactants, pigments, dyes, ultraviolet absorbers, light stabilizers, surface modifiers, antifoaming agents, wetting agents, dispersants, viscoelasticity modifiers, thixotropy-imparting agents, antiseptics, film-forming agents, plasticizers, penetrants, perfumes, bactericides, fungicides, ultraviolet absorbers, antioxidants, antistatic agents, flame retardants, and matting agents.
- a surface modifier is preferred from the viewpoint of smoothing the coating film surface.
- the surface modifier include a polysiloxane derivative (C).
- Examples of the polysiloxane derivative (C) include compounds having a polydimethylsiloxane skeleton.
- a polyether-modified polydimethylsiloxane is preferred, and in particular, a polyethylene oxide (or polypropylene oxide) addition polydimethylsiloxane is preferred.
- the content of the polysiloxane derivative (C) is, for example, from 0.1 to 0.5 parts by weight relative to 100 parts by weight of a total of the polyol compound (A) and the isocyanate compound (B).
- the content of the inorganic particle or the additive in the composition of the present disclosure is not particularly limited but is preferably 10 wt. % or lower relative to a total weight (100 wt. %) of non-volatile content of the composition.
- the solvent is represented, for example, by Formula (3):
- R 4 and R 6 each identical or different, represent a hydrogen atom or an alkyl group having from 1 to 5 carbon atom(s), R 5 represents an alkylene group having from 1 to 5 carbon atom(s), s represents an integer of 1 or greater, t represents 0 or 1, and when s is an integer of 2 or greater, each of a plurality of R 5 may be identical or different.
- alkyl group having from 1 to 5 carbon atom(s) in R 4 and R 6 examples include linear or branched alkyl groups, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an iso-butyl group, a s-butyl group, a t-butyl group, and a pentyl group.
- Examples of the alkylene group having from 1 to 5 carbon atom(s) in R 5 include examples similar to those for L 2 in Formula (1a).
- Examples of the solvent represented by Formula (3) include mono or poly(oxy C 1-6 alkylene) glycols, such as ethylene glycol, propylene glycol, butylene glycol, 1,3-butanediol, 1,4-butanediol, 1,6-hexanediol, diethylene glycol, and triethylene glycol; mono or poly(oxy C 1-6 alkylene) glycol mono(C 1-4 alkyl ether)s, such as ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monopropyl ether, and dipropylene glycol monobutyl ether; mono or poly(oxy C 1-6 alkylene) glycol di(C 1-4
- the solvent represented by Formula (3) is preferably a mono or poly(oxy C 1-6 alkylene) glycol mono(C 1-4 alkyl ether) mono(C 1-4 alkyl ester), and particularly a mono or poly(oxyethylene) glycol monoethyl ether monoacetate from the viewpoint of high solubility and excellent handleability.
- a different solvent other than the solvent represented by Formula (3) above may be used in the composition of the present disclosure.
- the different solvent include ester-based solvents, such as acetate esters (such as ethyl acetate and butyl acetate); ether-based solvents, such as dioxane and tetrahydrofuran; ketone-based solvents, such as acetone; aromatic solvents, such as toluene and xylene; halogen-based solvents, such as dichloromethane and chloroform; alcohol-based solvents, such as methanol, ethanol, isopropanol, and butanol; and nitrile-based solvents, such as acetonitrile and benzonitrile. These can be used alone, or in a combination of two or more.
- the content of the solvent (e.g., the solvent represented by Formula (3)) in the composition of the present disclosure is set to give a solid content concentration in the composition in a range from, for example, 70 to 99 wt. % (preferably 80 to 95 wt. %).
- the content of the solvent is preferably from 5 to 20 parts by weight, more preferably from 7 to 17 parts by weight, and even more preferably from 9 to 15 parts by weight relative to 100 parts by weight of a total of the polyol compound (A) and the isocyanate compound (B).
- composition of the present disclosure can be produced by mixing the above components.
- the composition of the present disclosure is preferably used as a two-component coating agent, where the polyol compound (A) and the isocyanate compound (B) are preferably separately stored and mixed at the time of use.
- composition of the present disclosure has the above configuration, and thus subjecting the composition to heat treatment enables the polyol compound (A) and the isocyanate compound (B) to be urethane-bonded to form a cured product (i.e., a cured product including a polyurethane resin).
- the heat treatment conditions are, for example, at 100 to 150° C. for approximately 0.5 to 12 hours.
- the cured product may be further aged at a temperature of room temperature (from 1 to 30° C.) for approximately 12 to 60 hours.
- the cured product thus obtained has excellent adhesion to a substrate (e.g., a plastic substrate, such as those of PET) and excellent scratch resistance.
- a substrate e.g., a plastic substrate, such as those of PET
- the cured product has a high hardness, and the pencil hardness (by a method in accordance with JIS K5600) of, for example, H or higher, preferably 2H or higher, particularly preferably 3H or higher, and even more preferably 4H or higher.
- the Martens hardness of the cured product is, for example, higher than 5.0 and 75.0 or lower, and preferably from 5.3 to 60.0.
- the cured product has excellent chemical resistance; for example, a sunscreen adhered to the cured product does not make the surface swell, or cause white cloudiness to occur. That is, the cured product has excellent sunscreen resistance.
- the cured product has the above properties in combination.
- the composition for forming the cured product is suitable as a coating agent for plastic molded products, such as extrusion-molded products, injection-molded products, and compression-molded products; and as a material for molded products, such as films.
- the plastic molded product include parts for constituting housings of home electric appliances (such as refrigerators, washing machines, air conditioners, and television sets), housings of electronic devices (such as personal computers, mobile phones, and smartphones), and parts for constituting musical instruments (such as pianos, electronic organs, and electronic musical instruments); and parts for vehicles, such as automobiles and railway vehicles, (interior materials, such as instrument panels, door trims, headlinings, and tonneau covers; and exterior materials, such as bumpers).
- examples of the plastic forming the plastic molded product include thermoplastic resins and thermosetting resins.
- thermoplastic resin examples include polyolefin-based resins, such as polyethylenes and polypropylenes; styrene-based resins, such as polystyrenes; polyesters, such as poly(ethylene terephthalate)s (PETs); vinyl chloride-based resins, such as vinyl chloride resins; polyamides, such as polyamide 46, polyamide 6, polyamide 66, polyamide 610, polyamide 612, polyamide 1010, polyamide 1012, polyamide 11, polyamide 12, and polyamide 1212; poly(phenylene ether)s, such as poly(2,6-dimethyl-1,4-phenylene ether); homopolymers or copolymers of acrylonitrile, such as PAN resins, AS resins, ABS resins, AAS resins, ACS resins, AES resins, and AXS resins; and (meth)acrylic resins, polycarbonates, polyacetals, poly(phenylene sulfide)s, poly(ether ether)
- thermosetting resin examples include phenol resins, urea resins, melamine resins, unsaturated polyesters, furan resins, epoxy resins, polyurethanes, allyl resins, and polyimides.
- a plastic molded product formed from a coating including the cured product of the present disclosure on at least a portion of the surface has excellent scratch resistance, chemical resistance, and the like.
- the thickness of the coating is not particularly limited and is, for example, approximately from 20 to 150 ⁇ m.
- the plastic molded product formed using the composition itself as a material has a surface including the cured product and thus likewise also has excellent scratch resistance, chemical resistance, and the like.
- the concentration of the residual ⁇ -caprolactone was determined to be less than 1.0% by gas chromatographic analysis, and then the mixture was cooled and taken out of the five-neck flask.
- the resulting compound (a1-1) had a number average molecular weight (Mn) of 611, a molecular weight dispersity (Mw/Mn) of 1.2, and a viscosity of 14.3 [Pa ⁇ s/25° C.].
- the number average molecular weight (Mn) and weight average molecular weight (Mw) were determined by comparison with polystyrene standards using a high-speed GPC apparatus, and the molecular weight dispersity (Mw/Mn) was calculated.
- the measurement conditions were as follows.
- Measuring apparatus a high-speed GPC apparatus “HLC-8220GPC”, available from Tosoh Corporation
- a polyol compound (A), an isocyanate compound (B), a surface modifier, and a solvent were placed as described in Table 1, mixed, and defoamed.
- the resulting composition was applied to a polyethylene terephthalate film (Cosmoshine A4100 #100, available from Toyobo Co., Ltd.) to give a coating thickness of 90 ⁇ m using an applicator, cured and dried in an oven at 120° C. for two hours, further cured under constant temperature and humidity conditions of 23° C. and 50% RH for 48 hours, and a cured coating/PET film laminate was obtained accordingly.
- a polyethylene terephthalate film Cosmoshine A4100 #100, available from Toyobo Co., Ltd.
- compositions were obtained in the same manner as in Example 1 except that the formulations of the compositions were changed as described in Table 1.
- the cured coatings of the laminates obtained in the examples and comparative examples were evaluated for pencil hardness, Martens hardness, scratch resistance, and sunscreen resistance by the following methods.
- the pencil hardness of the surface on the cured coating side of the laminates obtained in the examples and comparative examples was evaluated by the method in accordance with JIS K5600. That is, the surface on the cured side of the laminate was rubbed with a pencil (pencil lead), and a laminate in which a scratch was observed on the surface was determined to be NG (poor). Specifically, the evaluation was performed using a pencil with a predetermined hardness, and when no scratch was made, another evaluation was performed with a pencil with a hardness one grade higher, and this operation was repeated. Once a scratch was observed, the laminate was re-evaluated with a hardness one grade lower, and when no scratch was observed, the laminate was evaluated again using a pencil with a hardness one grade higher.
- the hardness of the hardest pencil with which no scratch was made was determined as the pencil hardness of the cured coating.
- those laminates subjected to moisture control under a constant temperature and humidity chamber at 23° C. and 50% RH for 24 hours were used.
- Pencil for evaluation a “Pencil for Pencil Hardness Test” available from Mitsubishi Pencil Co., Ltd.
- the Martens hardness of the surface on the cured coating side of the laminates obtained in the examples and comparative examples was measured using a Shimadzu Dynamic Ultra-Micro Hardness Tester DUH-211 (available from Shimadzu Corporation).
- the Martens hardness is a value determined by the quotient of the test load and the surface area penetrated by an indenter and is an index of surface hardness.
- a scratch test was performed by attaching a steel wool (B-204, Bonstar for commercial use #0000) to a rubbing tester (Standard Model, available from Nippon Rika Industries Corporation) and reciprocating the steel wool (10 reciprocations or 20 reciprocations) on the coating with a load of 500 g applied.
- the initial gloss (60-degree gloss) (G 0 ) before the scratch test on the cured coating side surface and the gloss (60-degree gloss) (G 1 ) after 2 minutes of the scratch test were measured using a gloss meter (Gloss Meter VG7000, available from Nippon Denshoku Industries Co., Ltd.), and the scratch resistance was evaluated by calculating the retention rate of the gloss by the following equation.
- the laminate after scratching was allowed to stand under constant temperature and humidity conditions of 23° C. and 50% RH for 24 hours, and the gloss (60-degree gloss) (G 2 ) of the coating after standing was measured, and the scratch recovery was evaluated by calculating the retention rate of the gloss to the initial gloss (60-degree gloss, G 0 ) by the following equation.
- the entire surface on the cured coating side of a test specimen (rectangle, 2 cm 2 ) of the laminates obtained in the examples and comparative examples was brought into contact with 0.4 g of a sunscreen cream (“Ultra Sheer Dry-Touch SPF45” available from Neutrogena Corporation) weighed on a slide glass (contact area of the cured coating and the sunscreen cream: 0.1 g/cm 2 ).
- the entire cured coating was covered with a polyvinylidene chloride film, and the test specimen was allowed to stand in an oven at 80° C. for 5 hours, then the sunscreen cream was wiped off, and the adhesive state of the cured coating was evaluated according to the criteria below. The following indicates that a cured coating harder to peel off had better adhesion to a substrate.
- the cured test specimen was allowed to stand on a flat surface with the coating side surface of the cured test specimen on the back side, and the height (mm) of each vertex from the flat surface was measured. The total value for the heights of each of the vertex (four locations) was evaluated as a curl (mm).
- a sunscreen cream (“Ultra Sheer Dry-Touch SPF45” available from Neutrogena Corporation) in an amount of 0.025 g/cm 2 , and the laminate was allowed to stand in an oven at 50° C. for one hour. The sunscreen cream was then wiped off, and the appearance of the cured coating was evaluated according to the following criteria.
- the cured coatings for Comparative Examples 1 and 2 obtained using a triol having no isocyanurate skeleton in place of the polyol compound (a1) were rated excellent for scratch resistance but poor or slightly poor for sunscreen resistance (adhesiveness), exhibiting poor adhesion.
- the cured coatings for Comparative Examples 3 to 6 obtained using only the polyol (a2) as the polyol compound (A) without using the polyol compound (a1) were rated poor or slightly poor in any of the evaluations of scratch resistance and sunscreen resistance, exhibiting insufficiency in any of adhesion, scratch resistance, or chemical resistance.
- a1-1 a compound (a1-1) obtained by Synthesis Example 1
- Solvent diethylene glycol monoethyl ether acetate, a reagent available from Tokyo Chemical Industry Co., Ltd.
- a polyol (a2) in an amount ranging from 0.01 to 1.5 parts by weight relative to 1 part by weight of the compound (a1), the polyol (a2) having a hydroxyl value (KOH mg/g) from 30 to 300.
- composition according to [11] The composition according to [10], in which the polyol (a2) is at least one selected from a polyester polyol, a polyether polyol, and a polycarbonate polyol.
- composition according to [12] The composition according to [10], in which the polyol (a2) is at least one selected from a polyester polyol and a polycarbonate polyol.
- the at least one isocyanate compound being selected from: 1,6-hexamethylene diisocyan
- composition according to any one of [1] to [21], in which an equivalent ratio of an NCO group contained in the isocyanate compound (B) to an OH group contained in the polyol compound (A), that is NCO/OH, is in a range from 0.2 to 2.0 (preferably from 0.5 to 1.5, more preferably from 0.7 to 1.3, and even more preferably from 0.9 to 1.2).
- a polydimethylsiloxane skeleton preferably a polyether-modified polydimethylsiloxane and more preferably a polyethylene oxide addition polydimethylsiloxane.
- the solvent represented by Formula (3) is at least one selected from: ethylene glycol monoethyl ether acetate; ethylene glycol monopropyl ether acetate; ethylene glycol monobutyl ether acetate; diethylene glycol monoethyl ether acetate; diethylene glycol monobutyl ether acetate; propylene glycol monoethyl ether acetate
- composition according to any one of [1] to [28], which is a coating agent is a coating agent.
- a plastic molded product having at least a portion of a surface being covered with a coating including the cured product described in [30].
- the composition of the present disclosure forms a cured product having excellent adhesion to a substrate, hardness, scratch resistance, and chemical resistance, and thus using the composition as a coating agent to cover a substrate enables the substrate to have the properties described above.
- the plastic molded product having at least a portion of its surface is covered with the cured product of the composition of the present disclosure has high surface hardness, excellent scratch resistance and chemical resistance.
- touching the plastic molded product, for example, with a hand to which sunscreen has been applied does not peel off or whiten the plastic cured product covering its surface, and the plastic molded product retains excellent appearance, adhesion, hardness, and scratch resistance over a long period of time.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2019168879A JP7340394B2 (ja) | 2019-09-17 | 2019-09-17 | 組成物及びその硬化物 |
JP2019-168879 | 2019-09-17 | ||
PCT/JP2020/034443 WO2021054256A1 (ja) | 2019-09-17 | 2020-09-11 | 組成物及びその硬化物 |
Publications (1)
Publication Number | Publication Date |
---|---|
US20220389149A1 true US20220389149A1 (en) | 2022-12-08 |
Family
ID=74877789
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US17/760,980 Pending US20220389149A1 (en) | 2019-09-17 | 2020-09-11 | Composition and cured product of same |
Country Status (7)
Country | Link |
---|---|
US (1) | US20220389149A1 (ja) |
EP (1) | EP4032927A4 (ja) |
JP (1) | JP7340394B2 (ja) |
KR (1) | KR20220064995A (ja) |
CN (1) | CN114402034A (ja) |
TW (1) | TW202120579A (ja) |
WO (1) | WO2021054256A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN113831449A (zh) * | 2021-10-29 | 2021-12-24 | 清远高新华园科技协同创新研究院有限公司 | 一种无溶剂丙烯酸树脂及其制备方法与应用 |
Family Cites Families (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS59157074A (ja) * | 1983-02-28 | 1984-09-06 | Daicel Chem Ind Ltd | 変性トリス(2−ヒドロキシエチル)イソシアヌレ−トの製造方法 |
JPS6047013A (ja) * | 1983-08-26 | 1985-03-14 | Asahi Glass Co Ltd | ウレタン変性ポリイソシアヌレ−トフオ−ムの製造方法 |
US4471102A (en) * | 1983-11-04 | 1984-09-11 | Textron, Inc. | Storage stable one component urethane compounds and method for making and using same |
JPS61243823A (ja) * | 1985-04-23 | 1986-10-30 | Dainippon Ink & Chem Inc | 高分岐ポリエステルエ−テル共重合体ならびにそれを含んで成る硬化性組成物 |
JP2964267B2 (ja) * | 1990-09-20 | 1999-10-18 | ダイセル化学工業株式会社 | 紫外線硬化型多官能ウレタンアクリレート |
JP3334152B2 (ja) * | 1992-03-30 | 2002-10-15 | 大日本インキ化学工業株式会社 | 光ファイバー被覆用樹脂組成物 |
DE10334723A1 (de) * | 2003-07-30 | 2005-02-24 | Bayer Materialscience Ag | Neue Bindemittelkombination für hochbeständige Kunststofflacke |
JP5614537B2 (ja) | 2009-12-01 | 2014-10-29 | 関西ペイント株式会社 | 耐チッピング性塗料組成物 |
JP5626795B2 (ja) * | 2011-03-11 | 2014-11-19 | 関西ペイント株式会社 | 複層塗膜形成方法 |
JP5630833B2 (ja) * | 2011-06-22 | 2014-11-26 | 関西ペイント株式会社 | 塗料組成物および該塗料組成物を用いた塗膜形成方法 |
JP2019168879A (ja) | 2018-03-23 | 2019-10-03 | カルチュア・コンビニエンス・クラブ株式会社 | 装置、方法、およびプログラム |
-
2019
- 2019-09-17 JP JP2019168879A patent/JP7340394B2/ja active Active
-
2020
- 2020-09-11 US US17/760,980 patent/US20220389149A1/en active Pending
- 2020-09-11 WO PCT/JP2020/034443 patent/WO2021054256A1/ja unknown
- 2020-09-11 KR KR1020227012277A patent/KR20220064995A/ko unknown
- 2020-09-11 CN CN202080065363.7A patent/CN114402034A/zh active Pending
- 2020-09-11 EP EP20864612.5A patent/EP4032927A4/en active Pending
- 2020-09-15 TW TW109131681A patent/TW202120579A/zh unknown
Also Published As
Publication number | Publication date |
---|---|
CN114402034A (zh) | 2022-04-26 |
EP4032927A1 (en) | 2022-07-27 |
WO2021054256A1 (ja) | 2021-03-25 |
JP7340394B2 (ja) | 2023-09-07 |
EP4032927A4 (en) | 2023-09-27 |
TW202120579A (zh) | 2021-06-01 |
JP2021046475A (ja) | 2021-03-25 |
KR20220064995A (ko) | 2022-05-19 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2020180760A1 (en) | Omniphobic polyurethane compositions, related articles, and related methods | |
CN111819253B (zh) | 膜形成用树脂组合物、层叠膜以及贴附有该层叠膜的物品 | |
WO2016125893A1 (ja) | 塗料用ウレタン樹脂組成物及び該組成物を用いた触感塗料 | |
US20220389149A1 (en) | Composition and cured product of same | |
KR102521247B1 (ko) | 소프트-필, 방오 코팅을 위한 폴리실록산-변형된 폴리우레탄을 포함하는 코팅 조성물 | |
EP3957668A1 (en) | Thermoplastic polyurethane composition for car interior surface material, and preparation method therefor | |
JP5741951B2 (ja) | 塗料組成物 | |
JP7420513B2 (ja) | 組成物及びその硬化物 | |
JP6927454B2 (ja) | ウレタン樹脂組成物及びフィルム | |
US11859044B2 (en) | Polyisocyanate compound, polyurethane resin forming composition using same, and cured product of said composition | |
JP7172893B2 (ja) | 熱硬化性コーティング剤、硬化物及びフィルム | |
WO2022075322A1 (ja) | 硬化性組成物及びその硬化物 | |
EP4318098A1 (en) | Spectacle lens and method for manufacturing same | |
JP2023064932A (ja) | 熱硬化性樹脂組成物、フィルム、フィルムを備えた物品 | |
JP2023121219A (ja) | ポリウレタン組成物、およびそれを用いてなる硬化膜、積層体、ならびにポリウレタンの非アミド系有機溶剤溶液 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: DAICEL CORPORATION, JAPAN Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNORS:KONNO, TAKASHI;MAETSU, NARITOSHI;WATANABE, JUN;AND OTHERS;SIGNING DATES FROM 20220304 TO 20220307;REEL/FRAME:059301/0704 |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: DOCKETED NEW CASE - READY FOR EXAMINATION |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: NON FINAL ACTION MAILED |
|
STPP | Information on status: patent application and granting procedure in general |
Free format text: RESPONSE TO NON-FINAL OFFICE ACTION ENTERED AND FORWARDED TO EXAMINER |